Kevin “Squid” Bolger started as a messenger in New York in 1992 and co-founded CycleHawk Messengers in 2007. “We probably went into business at the worst possible time,” he said. “I didn’t agree with it but I understood why bigger companies seemed to take advantage of people,” he said, citing workman’s compensation as an example of the kind of overhead that can leave companies little choice but to accept an offer to be acquired by someone bigger or to fold outright.

This year Cyclehawk started working with Zipments, a communication platform for couriers and customers. With E-commerce rushing towards same day delivery, tech companies are realizing that the bike messenger is still the best way to get product around in urban areas. “I’m excited for the rise in urban cycling,” he said. “I think the car culture’s kind of coming to and end, and the younger generation is seeing that cars don’t make sense. If you’re working with bikes, business is probably gonna grow.”

•••

TCB Courier in San Francisco is on the lookout for new ways to grow. When Nextel, the company they had used to set up communication between riders, reduced service in the city in May of 2012, TCB switched to another service provider and encountered similar problems. It soon became clear that they would need to move to an app-based system to track
deliveries. So they made their own.

The app helps TCB riders dispatch jobs to each other and stay on top of what’s going on with all of the company’s 40-and-counting clients. The plan, says Alex Farioletti an owner-rider at the company, is to eventually test the app in new cities. “This is gonna get weird,” Farioletti said about the intersection between the city’s technology and delivery sectors. And weird could mean good.

Since the company was founded in 2009, they’ve seen new services like Taskrabbit and Zipments make inroads in the expanding market of delivering food and other items from businesses that, just a few years ago, might have relied much more heavily on a physical retail outlet.

But there’s no substitute for experienced, professional bike messengers with the skill set needed to handle a high volume of time-sensitive runs. So TCB is looking at expanding the market they serve to facilitate some of this shift from retail to home and office delivery, bringing the expertise they’ve honed and their staff of 30 riders with them.

“We’re always hiring. We’re expanding steadily and we could be expanding even faster but it gets hard to get the caliber of riders we need to work for us,” said Farioletti. Another owner-rider, Trevor Beanes, estimates that they do 200-300 deliveries on an average day, using their current model of primarily doing food delivery for local restaurants.

Much smaller-scale operations are popping up outside the big, dense cities with histories of working bike messengers or strong bicycle commuting cultures. Kansas City, MO had no bike delivery businesses when Rudy Gonzales started Cowtown Couriers earlier this year. He says he envisioned the service partly as a way to help link the recent influx of new residents in downtown Kansas City with amenities only available in outlying parts of the city. If something isn’t available downtown (or anywhere else in Cowtown’s 14 square mile delivery zone), Gonzales or his business partner, Joshua Carney, are on call to deliver it by bike from 8 am to 5 pm during the work week, with plans to hire more riders and provide 24-hour service.

So far, they’ve gotten a lot of odds and ends or grocery runs for individual customers and also the occasional document for an architecture or design firm. Gonzales told me a lot of his business comes